1. Field of the Invention
This invention pertains to a method for flavoring an ingestible composition which comprises admixing an ingestible vehicle with an organoleptically effective amount of furfuryl propyl disulfide represented by the formula, (2-Furan-CH2SSCH2CH2CH3), in purified form, unaccompanied by substances of natural origin present in cooked beef and onions. The flavoring agent may be used in a wide variety of ingestible vehicles to augment or enhance the aroma or taste of foodstuffs, particularly roasted nut, roasted meat, beef broth, black pepper, onion, fine herbs, omelet, and cooked onion omelet flavored foodstuffs. The present invention also pertains to an ingestible composition comprising an ingestible vehicle and an organoleptically effective amount of the purified flavoring agent. The present invention also pertains to furfuryl propyl disulfide represented by the formula, (2-Furan-CH2SSCH2CH2CH3), in purified form, unaccompanied by substances of natural origin present in cooked beef and onions, and to methods for preparing furfuryl propyl disulfide.
2. Description of the Background
The Generessence(copyright) flavor research program conducted by Bush Boake Allen focuses on developing flavors by employing in depth understanding of the volatile organic components present in a wide variety of samples, for example fruits, herbs, and meat products and coupling this information to flavor preference profiling. A number of sampling and analytical techniques are used including extraction, distillation, and headspace analysis of the sample. The flavors are primarily formulated from synthetic chemicals and contain only components identified in the sample. There is no limit to the concentration of individual components used apart from organoleptic considerations. A problem with developing flavoring agents, such as cooked beef and onions flavor, is that natural flavoring agents do not contain a single flavoring agent, but rather contain a complex mixture of volatile components making identification of characteristic flavors very difficult.
U.S. Pat. No. 3,803,172 (Van Der Wal) discloses substituted tetrahydrofurfuryl and tetrahydrothienyl compounds having two mercapto substitutents at the 3-position. Preferred tetrahydrofurfuryl and tetrahydrothienyl compounds include (2-methyl-3-mercapto-tetrahydrofuryl-3) (2xe2x80x2-methyl-4xe2x80x2,4-dibydrofuryl-3xe2x80x2) sulfide; (2-methyl-3-mercapto-tetrahydrofuryl-3) (2xe2x80x2-methyl-2xe2x80x2,5xe2x80x2 dihydrofuryl-3xe2x80x2) sulfide; 2xe2x80x2,3-dimethyl-3xe2x80x2,4-dioxa-2,8-dithiabicyclo-{3,3,0}octanspirocyclopentane; 2xe2x80x2,4-dimethyl-3xe2x80x2,5-dioxa-2,8-dithiabicyclo{3,3,0}-octan-spirocyclope (2,5-dimethyl-3-mercaptotetrahydrofuryl-3) (2,5xe2x80x2-methyl4xe2x80x2,5xe2x80x2-dihydrofuryl-3xe2x80x2) sulfide; (2,5-dimethyl-3-mercapto-tetrahydrofuryl-3) (2xe2x80x2,5xe2x80x2-dimethyl-2,5xe2x80x2-dihydrofuryl-3xe2x80x2) sulfide; 2xe2x80x2,4,3,5-tetramethyl-3xe2x80x2,4-dioxa-2,8-dithiabicyclo{3,3,0}octanspirocyclopentane; 2xe2x80x2,4,4,6-tetramethyl-3xe2x80x2,5-dioxa-2,8-dithiabicyclo{3,3,0}octanspirocyclopentane; (2-methyl-3-mercapto-tetrahydrothienyl-3) (2xe2x80x2-methyl-4xe2x80x2,5xe2x80x2-dihydrothienyl-3xe2x80x2) sulfide; (2-methyl-3-mercapto-tetrahydrothienyl-3) (2xe2x80x2-methyl-2,5-dihydrothienyl-3xe2x80x2) sulfide; 2-methyl-2,3xe2x80x2,4,8-tetrathiablcyclo{3,3,0}octanspirocyclopentane; and 2xe2x80x2,4-dimethyl-2,3,5,8-tetra-thiabicycle{3,3,0}octanspirocyclopentane.
U.S. Pat. No. 3,917,869 (Evers et al. ""869) discloses a process for altering the organoleptic properties of a foodstuff which comprises adding to the foodstuff a substituted 3-furyl thioester compound to impart to the foodstuff a meaty aroma and taste. The substituted 3-furyl thioester is selected from the group consisting of 2,5-dimethyl-3-thio(2-ethylbutyryl)furan, 2-methyl-3-thio(2-ethylbutyryl)furan, and 2,5-dimethyl-3-thio(2-methylbutyryl)furan.
U.S. Pat. No. 3,982,038 (Evers et al. ""038) discloses a food flavor composition useful for augmenting the meaty or nutty flavor of a foodstuff comprising a 3-furyl xcex2-chalcogenalkyl sulfide. Preferred 3-furyl xcex2-chalcogenalkyl sulfides include (2,5-dimethyl-3-furyl) (2-mercapto-1-methyl propyl); (2,5-dimethyl-3-furyl) (2-hydroxy-1-methyl propyl); (2-mercapto 1-methyl propyl) (2-methyl-3-propyl) sulfide; (2-hydroxy-methyl propyl) (2-methyl-3-furyl) sulfide; trans-(2-hydroxy cyclohexyl) (2-methyl-3-furyl) sulfide; and trans-(2,5-dimethyl-3-furyl) (2-hydroxy cyclohexyl) sulfide.
U.S. Pat. No. 3,985,907 (Evers et al. ""907) discloses substituted 3-furyl beta-oxoalkyl sulfides. Preferred 3-furyl beta-oxoalkyl sulfides include (1,3-diethylacetonyl (2-methyl-3-furyl) sulfide; (2-methyl-3-furyl) (3,3,3-trimethyl acetonyl) sulfide; (2-methyl-3-furyl) (1-methyl-2-oxopropyl disulfide; (3-methyl-3-furyl) (1-methyl-2-oxopropyl sulfide; (1,3-diethylacetonyl) (2,5-dimethyl-3-furyl) sulfide; (camphor-3-yl) (2-methyl-3-furyl sulfide; and (2-methyl-3-furyl) (1,1,3,3-tetramethylacetonyl sulfide.
U.S. Pat. No. 3,985,908 (Evers et al. ""908) discloses substituted 3-furyl (2-pyridylmethyl) sulfides.
U.S. Pat. No. 3,993,792 (Winter et al. ""792) discloses a process for altering the natural flavor of soluble coffee which comprises adding a 2-substituted furfuryl compound. The 2-substitutent may be xe2x80x94(CH2)nSCOR, wherein R is hydrogen, methyl, ethyl, propyl, butenyl, or propenyl and n is 1 or 2; or xe2x80x94(CH2)nSR2, wherein R2 is methyl, propyl, isopropyl, or furfuryl and n is 0, 1, or 2; or xe2x80x94COSCH3. Preferred compounds include furfurylthiol acetate, furfurylthiol propionate, furfurylthiol butyrate, furfurylthiol xcex2, xcex2-dimethylacrylate, furfurylthiol tiglate, furfurylthiol formate, 5-methylfurfuryl methyl sulfide, furfuryl 5-methylfuryl sulfide, furfuryl isopropyl sulfide, 5-methylfuryl methyl sulfide, methylthiol furoate, furfuryl propyl sulfide.
U.S. Pat. No. 4,000,328 (Winter et al. ""328) discloses a soluble coffee material having a 2-substituted thiophene compound. The 2-substitutent is xe2x80x94(CH2)nCOR2, wherein R2 is methyl, ethyl, or propyl. Preferred compounds include 2-acetylthiophene, 3-methyl-2-acetylthiophene, 4-methyl-2-acetylthiophene, 3-methyl-2-propionylthiophene, 5-methyl-2-propionylthiophene, 2-butyrylthiophene, 5-methyl-2-acetylthiophene, 2-propionylthiophene, 2-acetylmethylthiophene, and 5,5xe2x80x2-diacetyldithienyl-2,2xe2x80x2-methane.
U.S. Pat. No. 4,007,287 (Evers et al. ""287) discloses a process for enhancing the flavor of a foodstuff comprising adding a 3-furfuryl sulfide compound. The 3-substitutent is a xe2x80x94SR1 group wherein in R1 is allyl. Illustrative examples include (allyl) (2-methyl-3-furyl) sulfide; (2-methyl-2-propenyl) (2-methyl-3-furyl) sulfide; (2-methyl-3-furyl) (methylthiomethyl) sulfide; (benzyl) (2-methyl-3-furyl) sulfide; and (2-butenyl) (2-methyl-3-furyl) sulfide.
U.S. Pat. No. 4,105,661 (Winter et al. ""661) discloses a 2-substituted pyrazine compound. The 2-substitutent is xe2x80x94(CH2)nxe2x80x94SR1 wherein n is 0, 1 or 2, R1 is hydrogen, methyl, ethyl, acetyl, or furfuryl. Illustrative examples include (2-methylpyrazinyl-3, -5 and -6) furfuryl sulfides; pyrazinylmethyl mercaptan; pyrazinylmethyl methyl sulfide; pyrazinylmethyl ethyl sulfide; pyrazinylmethyl furfuryl sulfide; pyrazinylmethylthiol acetate; 2-pyrazinyl-ethyl mercaptan; 2-pyrazinyl-ethyl methyl sulfide; 2-pyrazinyl-ethyl ethyl sulfide; 2-pyrazinyl-ethyl furfuryl sulfide, and 2-pyrazinyl-ethylthiol acetate.
U.S. Pat. No. 4,514,429 (Pittet et al.) discloses a process for augmenting the aroma or taste of a foodstuff comprising adding to the foodstuff a 2-substituted furfural compound. The 2-substituents are dipropyl mercaptal and substituted 1,3-dithiolanes.
While the above disclosures provide some insight into the flavoring components in cooked beef and onions, the above disclosures do not provide satisfactory cooked beef and onions flavoring agents. The present invention provides a novel flavoring agent without the disadvantages which are characteristic of previously known products. The present invention also provides methods for preparing and using the flavoring agents and the ingestible compositions in which it may be employed.
The present invention is directed at a method for flavoring an ingestible composition which comprises admixing an ingestible vehicle with an organoleptically effective amount of furfuryl propyl disulfide represented by the formula, 2-Furan-CH2SSCH2CH2CH3, in purified form, unaccompanied by substances of natural origin present in cooked beef and onions.
The present invention is also directed at an ingestible composition comprising (i) an ingestible vehicle; and (ii) an organoleptically effective amount of furfuryl propyl disulfide represented by the formula, 2-Furan-CH2SSCH2CH2CH3, in purified form, unaccompanied by substances of natural origin present in cooked beef and onions.
The present invention is further directed at furfuryl propyl disulfide represented by the formula, 2-Furan-CH2SSCH2CH2CH3, in purified form, unaccompanied by substances of natural origin present in cooked beef and onions.
The present invention is still further directed at a method for preparing furfuryl propyl disulfide represented by the formula, (2-Furan-CH2SSCH2CH2CH3), which comprises reacting sodium furfurylthiolate with sodium propylthiosulfate to yield furfuryl propyl disulfide.